Dialdehyde compound and process for making same



(Condensate oi stearic acid amide and monomeric giyoxal) Patented Oct. 6, 1942 UNITED STATE PATENT OFFICE DIALDEHYDE COMPOUND AND PROCESS FOR MAKING SAME Hans Beck, Krefeld,

lein Patent Corporation,

poration of New York application May 22, 1937, Divided and this applica- No Drawing. Original Serial No. 144,304.

tion April 11, 1939, Serial No.

many May 2'7, 1936 9 Claims.

R.CO.NH.CH2O, (R.C0.NH)2CH, aconncmo aryl, R1.NH.CH2Q, and

and R is selected from the group consisting of an aliphatic radical and a naphthenic radicaLR is, an aliphatic radical, and R contains an aliphatic radical. This radical may be combined with one or more cyclic groups as found, for example, in the members of the sterolor wool fat group. Each of said radicals R, R and R contains at least 10 carbon atoms. The said products are particularly useful, for instance, in producing water-repellence in textiles and other materials as set forth in said above-mentioned patent, but their use is not restricted thereto.

The principal objects of the present invention accordingly are to provide a series of useful compounds of the type mentioned and to produce simple efficient processes for the manufacture of such compounds. In order that the nature of Germany, assignor to Heber- New York, N. 2., a cor- 267,339. In Gel- Or reaction with two molecules of the acid amide is as follows;

CnHsaC ONH: H /H C 11H. C ONE: 0 O

I (2 mols stearic acid amide)+(Monomcric-glyoxol) C17H35.C ONE O C\ +H: 0

CnHanC ONE (Condensate of 2 mols stearic acid amide and monomeric glyoxal) (2) Reaction with an amine is as follows:

these reaction products may be better under-' stood, the following represent typical examples of reactions of dialdehydes with the substances mentioned although it will be understood that these reactions are given purely for illustrative purposes and that the invention is not to be considered as restricted thereto except as indicated in the appended claims. The reactions are:

HH C11Hu.CONHz+0=( 3.( }'=O-) (Stoaric acid amide) (Monomeric glyoxal) .cumrconmcmoo o H H CnHar-NH: O=l-=O-) (Stearyl amino) (Monomeric glyoxal) H .o +Hci-- o (Octadecyl alcohol)+(Monomeric-glyoxal) (Di-octadecyl scmi acetal of glyoxal) (4) Substances which we have successfully made in accordance with my invention, in addition to the above, include the following:

The reaction product of stearic acid amide and polyglyoxal. The formulae for the reaction products combination of one and two mols of stearic acid amide with monomeric glyoxal.

are the same as given above for the terephthalic aldehyde:

The reaction product of palmitic acid amide and polyglyoxahhaving the formulae:

(With 1 mol of palmitic acid amide) Cami-C ONH H H .C cumrcon o (With 2 mols oi palmitic acid amide) The reaction product 01 stearic acid amide and CnI-BaCONH:

are dissolved in 1 liter of carbon tetrachloride and there are added thereto 58 grams of monomeric-glyoxal H H O=.( J=O The mixture is heated for about 30 minutes to 70 C. (158 F.). With decoloration of the solution the dialdehyde reaction product having a straight chain of more than 10 carbon atoms is formed. 1

Example 2.58 grams of polyglyoxal are introduced into 600 grams of acetic acid anhydride, and the mixture is heated to 120 C. (248 F.) To the solution there are then added 248 grams of stearic acid amide CrzHzsCONH:

whereupon the formation of the dialdehyde reaction product having a straight chain of.more than 10 carbon atoms takes place with decoloration of the solution.

Example 3.58 grams of polyglyoxal are dissolved in 120 cu. cm. of water and are stirred together with 260 grams of palmitic acid amide C15Ha1.CO.NHz

to form the dialdehyde reaction product having a straight chain of more than 10 carbon atoms. The paste is then dried and subjected for 2 hours to a temperature of 110 C. (230 F.).

Example 4.-134 grams of terephthalic aldehyde H /H 0 0/ g \0 are dissolved in 1 liter of carbon tetrachloride and to it there are added 284 grams of stearic acid amide CrrHssCONH:

The mixture is heated for a time. A dialdehyde reaction product having a straight chain of more than 10 carbon atoms 01' high molecular weight is formed. The productis:

H o11Hu.coNn.on,0.o.mo

0 Example 5.-270 grams of octadecyl alcohol are dissolved in 2 liters of benzine, 30 grams of monomeric glyoxal acetal of glyoxal 1:11:10) CH.C

In place of stearic acid amide and palmitic acid amide other aliphatic amides may be employed, for instance lauric acid amide, montanic acid amide, naphthenic acid amide may be employed. Instead of these amides, amines may be employed such as stearyl amine or mixtures of primary saturated amines which are obtained by the hydration of train oils, for example as described in D. R. P. 611,924 or French Patent No. 761,952. In place of the amides or amines, alcohols may be employed such as octadecyl a1- cohol, myricyl alcohol, etc. The production of the aldehydes from amines and alcohols is effected in the same manner as from the amides and presents no peculiarity.

While the invention has been described in detail according to the preferred manner of carrying out the process, it will be obvious to those skilled in the art after understanding the invention, that changes and modifications may be made therein without departing from the spirit and scope of the invention, and it is intended to cover all such changes and modifications.

What is claimed as new and desired to be secured by Letters Patent is:

1. A new substance having the formula Y.OHO, where Y is a member selected from the group consisting of R.CO.NH.CH:O, (R.CO.NH) 20H, R.CO.NH.CH:O aryl, R .NH.CH2O, and (12. .0) 201-! and R is selected from a group consisting of aliphatic radicals and naphthenic radicals, R is an aliphatic radical, and R3 contains an aliphatic radical, each of said radicals R, R and R. containing at least 10 carbon atoms.

2. .As a new substance, the product of reaction 4. A process of the kind described which comprises reacting polyglyoxal with stearic acid amide to produce a product of condensation of stearic acid amide with polyglyoxal.

5. A process of the kind described which comprises reacting terephthalic aldehyde with stearic acid amide to produce a product of condensation of stearic acid amide with terephthalic aldehyde.

6. As a new substance, 9. condensate of stearic acid amide and monomeric glyoxal having the iormula 0171135. C ON H CnHwC ONE 7. As a new substance, a condensate of stearic acid amide with polyglyoxal having the formula 8. A process of the kind described which comprises combining a dialdehyde with a material selected from the group consisting of an aliphatic amide, a naphthenic amide, an aliphatic amine, an alcohol containing an aliphatic radical, each of which contains a radical having at least 10 carbon atoms, said aliphatic radicals having said carbon atoms in a straight chain, and producing a condensate of said dialdehyde through one aldehyde group with the said radical having at least 10 carbon atoms.

9. A process of the kind described which comprises combining monomeric glyoxal with a material selected from the group consisting of an aliphatic amide, a naphthenic amide, an aliphatic amine, and an alcohol containing an aliphatic radical, each of which contains a radical having at least 10 carbon atoms, and pro- I CER'I'I1?ICATE OF commczuon. Patent No. 2,297,831.. October 6, 19 42.

' ms BECK;

It is hereby certified that error appeara 1n the printed specification 0; the Ibo v0 nunberd pafiont requiring correction as follows; Page 1, first colmh, line 7 for-the word 'may' read -vhich"; page 2, first column, line L6, for "211.8 grams" read "281'. grams-- and that the a aid Lefitera Patent should be read with thia'oorroction thereinthat the some may conform to the record 01 the. case in the patent Office.

si ned and sealed this 10th day of November, A. n. 1942.

Henry Van Arsdnle, (Soa1)' Acting ccmmiasionr of Patents. 

